Costumes are great for letting out your inner dark desires. Link/Tentacle monster roleplay
Coming to the anime convention as a tentacle monster might have been the best idea she ever had, Rosalyn thought as she came upon the young man dressed as Link. They were on a mostly deserted corridor of the hotel, a laptop counter area that was very randomly on one of the upper levels near some rooms. If anyone heard them they would probably assume it was just their neighbors.
“Do you understand how often Link gets raped by a tentacle monster on the internet?” She asked the possibly drunk, definitely cute, boy who was wedged under the counter tops with his bag of goodies.
He looked her over with big, brown eyes which widened upon seeing the large purple strap-on and mostly painted-on clothing (except for the lingerie of course). Rosalyn was wearing only a purple, lacy bra and panties, the rest was body paint that gave the illusion of purple tentacles with suction cups for all her limbs. Her hair was a bright and vibrant purple, and her smile was predatory.
“Are you going to? Rape me then?” Link asked placidly, half curious, half wary.
“I really, really want to.” She confided.
They just stared at each other for a few moments, locked in each others gaze. Rosalyn reach down to the thick purple dildo at her groin and rubbed it mock-idly. She watched him and she stroked “herself”. His eyes darted from her eyes to the motion, and then back to her eyes, his wider then ever before, if that were possible. He licked his lips and began to move forward. She watched him, eyes narrowed. Would he walk away? He'd have to pass her if he left the little area, should she stop him?
Rosalyn took the initiative and before she could accurately tell his intention, she took the required two steps forward and pushed the tip of the dildo against his lips. He gasped and when his mouth opened she pushed it a little bit in and then out again. He looked up at her, eyes wide and scared. She got a grip on his blonde hair (actually his own) and pushed the dildo back into his mouth. He submitted, opening his lips and allowing it to reach the back of his throat and he gagged. He pushed against her hips to be let go, squeezing his eyes shut and making half-slaps at her skin, but she made him pull back slowly, eventually extracting the dildo from his mouth with a gentle pop. He gasped and those big eyes were watery and frightened as they looked up at her.
“Are you...Are you going to put it in my ass next?” he asked hoarsely.
“Tell me I can.” She commanded.
He breathed for a while, eyes scanning the floor, but not seeing. It was clear he was thinking hard.
Finally he met her eyes and nodded. She grinned.
“Then I guess I'm not raping Link after all.” Rosalyn said with a sultry chuckle, even though it might as well have been. Her dildo was huge, and she was willing to bet he was a virgin. But this was A-Kon, and he had the chance to get fucked by a tentacle futanari, even if he was afraid he couldn't turn that down. Not with no witnesses to even get a hint that he might do such a thing.
She tightened the grip on his hair and shoved him back down on the dildo again. He gagged and a single tear slid down his face. She surprised him by suddenly pushing his head to the ground.
“Keep your cheek pressed to the carpet, pet.” She ordered soothingly, before circling behind him and taking a good look at his now up-turned rear-end.
She yanked the leggings down unceremoniously, and spread his ass to take a good look at the hole she'd soon be violating. Link squeaked and she gave him a light spank.
“You're going to give it to me, so shut up and take it.” She said in an authoritative fashion. Link breathed heavily, but didn't resist. He even spread his legs a little.
Rosalyn dug into her bag and brought out the condoms and lube she'd brought mostly as a joke. She rolled one onto the dildo and squeezed out a large dollop onto her palm. She spread it thoroughly over the condom-clad dildo, then got out some more and began probing the young man's hole. She used one finger from each hand and he made little strangled noises as she did her best to stretch him.
“Now,” she began, lining the tip of her strap-on with his hole, “I'm going to fuck you. You are going to take it until I'm done with you. Understand?”
“I'm helpless Link.” He responded, maybe with tears in the voice, or maybe that was excitement, “You're not raping me, you're raping Link.”
Rosalyn grinned approvingly. She liked that. She plunged the dildo in with no warning and Link howled in surprise.
“Quiet.” she shamed him with a little smack on his rump.
“Yes, yes, I'm sorry.” He whispered, as though he were suddenly aware of where they were and that they might be caught.
Rosalyn reached around and fondled his sagging prick. The young man gasped and groaned, his body getting used to the intrusion and able to begin to appreciate the feeling of getting wanked. The feax-futanari waited until he began to thrust a little into the slightly lubed hand before deciding to continue the fucking.
She pulled out, deceptively slow, making sure he felt every inch be extracted. Then, without warning, she plunged back in. She fucked him like this, watching his face from above. He had one hand pressed against his mouth and the other around his substantially hardening cock. With every whimper and moan, Rosalyn felt a heated tingle in her clit. It throbbed, enticed, but not extinguished, by the pressure of every thrust. She knew she would have to fuck him harder, faster, in order to come like this, but she did not wish to be too cruel.
Rosalyn pulled the neon dildo from Link's body and peered at his gaping hole with wonder. It was disgusting and beautiful all at once. She had the sudden urge to lick it, but knowing it would be foul, suppressed the impulse. Instead she checked for signs of injury. There was no blood, though he was rather red and raw. More lube, perhaps.
“Are you- Are you finished?” Linked gasped out, still not taking his cheek off the floor like a good boy.
“Not just yet, darling.” Rosalyn soothed, squeezing more slickness on her dildo more hurriedly that she was willing to admit to.
“O-oh...” he whimpered, wiping spit from his drool mouth on his arm and breathing heavily, “I...”
“Hmm?” Rosalyn paused at his entrance.
“I...want it.” he told the carpet, what blood that hadn't rushed to his cock now climbing up his neck.
“I had noticed” the girl teased, reaching around to stroke his beautifully hard member, all the nervousness she had reacquired in their pause, swept away again by his declaration, “You're a dirty little whore, aren't you? You love to be forced into taking it! You love how big it is, you like how it hurts!”
He hiccuped and tried to lift his head and turn it so that she couldn't no longer see his face, but Rosalyn would not allow it.
“Cheek to the carpet, darling, remember?” she asked would-be sweetly, grabbing him by the hair to turn his head back to how it was.
Now she fucked him. Really fucked him. Without mercy or care she plunged the dildo into his body with the full force that her hips could muster. His frantic whimpering was getting louder and louder, so she shoved two fingers in his mouth and commanded him to suck. She spanked him, hard, with every thrust until his ass was flame red and too tender for there to be any pleasure, and then she kept spanking. Tears streamed down his cheeks, and the sight surged her on, fucking him faster and harder, the pressure in her clit reaching a fever pitch.
“pweath...” Link said, trying to plead with her around the fingers in his mouth, “it hurts...”
“Take it.” she grunted.
Rosalyn was getting close now. So close, that she abandoned the beating she was giving the boy to furiously rub at her clit. She made primal noises, fucking him with her full strength as she touched herself.
“Come.” she could have been commanding herself, as well as him.
He made a noise like he was trying to talk around the fingers again, but she shoved them deeper into his mouth and he gagged and then was quiet.
“Come.” she said again. “You stupid fucking whore! You come on this dick!”
Her frantic thrusts halted as she clenched up and came, gushing fluid into her lace undies. Link used the pause of pain and destruction of his asshole to pull at his still-hard dick until thick streams of cum sprayed the carpet.
Rosalyn pulled the dildo out of him and chuckled at the ruined mess she had caused. Link look ransacked, covered in spit and cum, his ass bright red and hole wide and gaping. He wasn't moving, laying in his own cooling liquids and breathing heavily. She grabbed her camera phone out of her bag and snapped a few pictures of the beautiful sight.
“Want a picture together?” she asked coyly, “it is A Con, after all.”